Copper plating bath composition and method for deposition of copper

Patent metadata

Field	Value
Publication number	US-10633755-B2
Application number	US-201615754008-A
Country	US
Kind code	B2
Filing date	Sep 9, 2016
Priority date	Sep 10, 2015
Publication date	Apr 28, 2020
Grant date	Apr 28, 2020

Abstract

The present invention relates to aqueous acidic plating baths for copper deposition in the manufacture of printed circuit boards, IC substrates, semiconducting and glass devices for electronic applications. The plating bath according to the present invention comprises at least one source of copper ions, at least one acid and an additive obtainable by a reaction of at least one aminoglycidyl compound comprising at least one amino group which bears at least one glycidyl moiety and at least one second compound selected from ammonia and amine compounds wherein the amine compounds comprise at least one primary or secondary amino group with the proviso that the aminoglycidyl compound contains at least one polyoxyalkylene residue and/or the amine compound contains at least one polyoxyalkylene residue. The plating bath is particularly useful for filling recessed structures with copper and build-up of pillar bump structures.

First claim

The invention claimed is:

1. An aqueous acidic copper electroplating bath which comprises at least one source of copper ions and at least one acid characterized in that the bath further comprises at least one additive obtained by a reaction of at least one aminoglycidyl compound and at least one compound selected from ammonia and amine compounds wherein the amine compounds comprise at least one primary or secondary amino group with the proviso that the aminoglycidyl compound and/or the amine compound contains at least one polyoxyalkylene residue.

2. The aqueous acidic copper electroplating bath according to claim 1 characterized in that the at least one aminoglycidyl compounds is selected from (A1) to (A5):

wherein
each R is a monovalent residue independently selected from the group consisting of hydrogen, aliphatics, nitrogen-containing aliphatics, aralkyl, aryl, hetaryl, polyoxyalkylene and combinations of the aforementioned;
A is an (a+b)-valent hydrocarbon residue and a and b are integers each ranging from 0 to 10 with the proviso that the sum of a and b ranges from 2 to 10,
or

wherein (A5) is a cyclic hydrocarbon optionally comprising further heteroatoms selected from nitrogen, sulphur and/or oxygen in the ring and which consists of 4 to 12 carbon and heteroatoms; and c is an integer ranging from 1 to 6.

3. The aqueous acidic copper electroplating bath according to claim 2 characterized in that the aminoglycidyl compound is selected from the group consisting of benzyl(glycidyl)amine, N-glycidyldiethylamine, diglycidylamine, diglycidylethylamine, diglycidylmethylamine, diglycidylamine, diglycidylmethylamine, diglycidylethylamine, triglycidylamine, 4,4′-methylenebis(N,N-diglycidylaniline), 1,3-bis-(N,N-Diglycidylaminomethyl)cyclohexane, 1,3,5-tris(2-oxiranylmethyl)-1,3,5-triazinane-2,4,6-trione, 1-glycidylpiperidine, 4-glycidylmorpholine, 4-glycidylthiomorpholine, 1-glycidylpiperazine, 1-glycidylim idazol, 1-glycidylpyrazol, 1-glycidylpyrrolidine, 1-glycidyl-2-pyrolidone, 1-glycidyl-2-pyridone, 2-glycidylpyridazin-3-one, 1-furfuryl(glycidyl)amine, furfuryl(glycidyl)amine, glycidyl(tetrahydrofurfuryl)amine, 4-glycidyl-1,4-thiazepane, 1-glycidylazepane, 1-glycidylbenzimidazole, 3-glycidylthieno[2,3-d]pyrimidin-4-one, 3-glycidylthieno[3,2-d]pyrimidin-4-one and the glycidyl, diglycidyl and oligoglycidyl derivatives of polyetheramines.

4. The aqueous acidic copper electroplating bath according to claim 3 characterized in that the amine compound is selected from alkylamines; dialkylamines; alkylarylamines; aralkylamines; alkylendiamines or higher homologues thereof having the overall structure of H—(NH-G) g -NH 2 wherein each G is an alkylene residue independently selected from each other G having 1 to 8 carbon atoms and g is an integer ranging from 1 to 6; cyclic non-aromatic amines of the following structure

wherein each J is hydrogen, —CH 2 —NH 2 or —CH 2 —CH 2 —NH 2 and r is an integer ranging from 3 to 6; arylamines; diarylamines; nitrogen-containing hetaryls with optional amine moieties bound to the hetaryl moiety; amino acids; polyetheramines; polyvinyl amines; polyallyl amines; polyethylene imines; guanidines; aminoguanidines; urea, alkylurea, dialkylurea; carbomoyl acid derivatives and esters thereof; amidinyl derivatives and salts and/or hydrates of any of the aforementioned.

5. The aqueous acidic copper electroplating bath according to claim 4 characterized in that the at least one second compound is an amine compound is selected from alkylamines, alkylendiamines or higher homologues thereof having the overall structure of H—(NH-G) g -NH 2 wherein each G is an alkylene residue independently selected from each other G having 2 to 5 carbon atoms and g ranges from 1 to 4, cyclic non-aromatic amines of the following structure

wherein each J is hydrogen, —CH 2 —NH 2 or —CH 2 —CH 2 —NH 2 and r is 3 or 4 with the proviso that only one or no J is other than hydrogen; arylamines; nitrogen-containing hetaryls with optional amine moieties bound to the hetaryl moiety; polyetheramines; aminoguanidines and salts and/or hydrates of any of the aforementioned.

6. The aqueous acidic copper electroplating bath according to claim 1 characterized in that the aminoglycidyl compound is selected from the group consisting of benzyl(glycidyl)amine, N-glycidyldiethylamine, diglycidylamine, diglycidylethylamine, diglycidylmethylamine, diglycidylamine, diglycidylmethylamine, diglycidylethylamine, triglycidylamine, 4,4′-methylenebis(N,N-diglycidylaniline), 1,3-bis-(N,N-Diglycidylaminomethyl)cyclohexane, 1,3,5-tris(2-oxiranylmethyl)-1,3,5-triazinane-2,4,6-trione, 1-glycidylpiperidine, 4-glycidylmorpholine, 4-glycidylthiomorpholine, 1-glycidylpiperazine, 1-glycidylim idazol, 1-glycidylpyrazol, 1-glycidylpyrrolidine, 1-glycidyl-2-pyrolidone, 1-glycidyl-2-pyridone, 2-glycidylpyridazin-3-one, 1-furfuryl(glycidyl)amine, furfuryl(glycidyl)amine, glycidyl(tetrahydrofurfuryl)amine, 4-glycidyl-1,4-thiazepane, 1-glycidylazepane, 1-glycidylbenzimidazole, 3-glycidylthieno[2,3-d]pyrimidin-4-one, 3-glycidylthieno[3,2-d]pyrimidin-4-one and the glycidyl, diglycidyl and oligoglycidyl derivatives of polyetheramines.

7. The aqueous acidic copper electroplating bath according to claim 6 characterized in that the amine compound is selected from alkylamines; dialkylamines; alkylarylamines; aralkylamines; alkylendiamines or higher homologues thereof having the overall structure of H—(NH-G) g -NH 2 wherein each G is an alkylene residue independently selected from each other G having 1 to 8 carbon atoms and g is an integer ranging from 1 to 6; cyclic non-aromatic amines of the following structure

wherein each J is hydrogen, —CH 2 —NH 2 or —CH 2 —CH 2 —NH 2 and r is an integer ranging from 3 to 6; arylamines; diarylamines; nitrogen-containing hetaryls with optional amine moieties bound to the hetaryl moiety; amino acids; polyetheramines; polyvinyl amines; polyallyl amines; polyethylene imines; guanidines; aminoguanidines; urea, alkylurea, dialkylurea; carbomoyl acid derivatives and esters thereof; amidinyl derivatives and salts and/or hydrates of any of the aforementioned.

8. The aqueous acidic copper electroplating bath according to claim 7 characterized in that the at least one second compound is an amine compound is selected from alkylamines, alkylendiamines or higher homologues thereof having the overall structure of H—(NH-G) g -NH 2 wherein each G is an alkylene residue independently selected from each other G having 2 to 5 carbon atoms and g ranges from 1 to 4, cyclic non-aromatic amines of the following structure

wherein each J is hydrogen, —CH 2 —NH 2 or —CH 2 —CH 2 —NH 2 and r is 3 or 4 with the proviso that only one or no J is other than hydrogen; arylamines; nitrogen-containing hetaryls with optional amine moieties bound to the hetaryl moiety; polyetheramines; aminoguanidines and salts and/or hydrates of any of the aforementioned.

9. The aqueous acidic copper electroplating bath according to claim 1 characterized in that the amine compound is selected from alkylamines; dialkylamines; alkylarylam

Assignees

• Atotech Deutschland Gmbh

Inventors

• Rohde Dirk
• Palm Jens

Classifications

• C25D3/38 Primary

  of copper · CPC title

• C25D3/58

  containing more than 50% by weight of copper · CPC title

• C25D7/12

  Semiconductors · CPC title

• C25D7/00

  Electroplating characterised by the article coated · CPC title